Five Rules for Asking a Guy Out

In your own mind, you may think you’re being unmistakably clear about your intentions.


There’s no easy way to phrase this without provoking a barrage of “What are you, crazy?” emails, but here’s my theory: By the time she hits 20, even the shyest, mousiest, most un-Katie-Holmes like woman has developed at least a rudimentary strategy for fending off (or responding to) unsolicited come-ons by eager guys. But unless a guy happens to look like Viggo Mortensen, he can persist well into his 40s without once having been — flatly, out of the blue — asked out on a date. (After that, the odds tend to shift, as those handsome, hard-driving captain-of-industry types die off or get married, resulting in a surplus of on-the-prowl single women. Have I offended anyone yet?)

 Anyway, whatever the explanation, the fact is that single women are more accustomed to being asked out, and single guys are more accustomed to doing the asking — which means there’s not a lot of data out there about how men like to be approached for a first date. With an eye toward correcting this imbalance, here are my observations about the best way to hit on a guy, whether it’s someone you work with, someone you’ve met online, or someone you’ve just rear-ended at a busy intersection.

Be direct. Guys are complete idiots (being a guy myself, I mean this in the nicest possible way). In your own mind, you may think you’re being absolutely, unmistakably clear about your intentions when you ask that adorable hipster in the next cubicle if he’d like to grab some Thai takeout for lunch, whereas he’s probably thinking something like “Thai... cool. I am kinda hungry.” Ask a guy out the way he’d ask you out: “Would you like to have dinner tonight?” is fairly hard to misinterpret, and “Would you like to come over to my place tonight and I’ll cook you dinner?” is even harder to misinterpret (though don’t put it past him to think something like, “Gee, that’s nice of her. She must have some salmon that’s about to spoil.”) 

Be indirect. Well, OK, here’s another approach to try: Remember how, back in junior high school, you’d ask your girlfriend to ask her sister if that cute, broody guy on your bus was going steady with anyone? This technique works well in adult life, too: The fact is, most guys were deeply unpopular in junior high school and will be flattered to have your friends do some advance scouting (just make sure your emissary isn’t on the market herself, lest you wind up recreating the plot of a Miley Cyrus movie). Really, there are worse things than having a friend go fishing on your behalf with a, “Hey, are you seeing anyone now...? I know someone who thinks you’re cute...” Note to guys: Based on my experience, this approach doesn’t work with grown-up women, who’d rather you show some guts and do your own legwork. 

Come up with a plan. Choose between the following two conversations. Conversation A: You, to that cute guy in the coffee shop: “Um, do you think you’d... maybe like to... go out sometime?” Cute guy in the coffee shop, to you: “Um... yeah... maybe we can do something... sometime.” Conversation B: You, to that cute sales clerk at Barnes & Noble: “Hey, Dave Eggers is giving a reading tonight at a really cool bar downtown. Would you like to go?” Cute sales clerk at Barnes & Noble, to you: “Sure!” Get the point? 

Don’t come on too strong. I’ll spare you the Freudian mumbo-jumbo about how, deep down, guys are actually scared of women, and their subconscious minds will transform an ostensibly breezy come-on (“Hey, Slim! What say I treat you to some steak and eggs at Denny’s?”) into a screaming nightmare about some woman in a caftan chasing them with a pair of oversized scissors. It’s unfair, I agree, but the way society is set up, men are much better able to get away with confident-bordering-on-arrogant bluster than women are. Be nice; use a gentle voice; smile. Approach the object of your desire as you would a timid bunny rabbit. 

Don’t over-plan. It’s only in sitcoms that guys hire skywriters and three-piece mariachi bands to announce their interest in cute, yet clueless, roommates. So don’t feel you should follow that tradition. Blue Angel flybys may be out of your price range, but even a gimmick as innocent-seeming as a homemade chocolate muffin accompanied by a written invitation is overdoing it... and may set off a man’s Obsessed radar. And you don’t have to invite the guy out for much more than some liquid refreshment. Just ask, plain and simple, the same way you’d ask for directions to the ladies’ room. “Would you like to have a cup of coffee/grab lunch sometime?” will work just fine. Frankly, most of us are so flattered that you’d request our company that we’re delighted to oblige. 


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